Journal of Organic Chemistry p. 5550 - 5556 (1985)
Update date:2022-08-03
Topics:
Silverman, I. Robert
Daub, Guido H.
Jagt, David L. Vander
The synthesis of 9-methoxy-4,5-dihydrobenzopyrene-4-13C4,5-oxide and -5-13C4,5-oxide and of 8-methoxy-4,5-dihydrobenzopyrene-4-13C4,5-oxide is reported.The compounds were synthesized in yields of 15percent each from unlabeled precursors. 13C NMR analysis of the conversion of the 4,5-oxides to 4-phenols and 5-phenols (NIH shift) revealed a very strong electronic effect of a 9-methoxy substituent, which gave only the 4-phenol, and a significant but weaker effect of an 8-methoxy substituent, which gave both phenols with the 5-phenol predominating.
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